Call us at (860) 909-8066 to learn more about active adult communities in Winsted
Winsted, CT 55+ active adult communities & homes for sale
78 communities near Winsted
130 homes near Winsted
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$100Ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$400Ks
- $500Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
Want to learn more about 55+ communities in Winsted, CT?
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$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$600Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
$400Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$400Ks
- $700Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
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4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
$600Ks
- $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
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$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$300Ks
- $400Ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
$400Ks
- $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$100Ks
- $200Ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500Ks
- $800Ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
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$500Ks
North Woods of Colchester, Colchester, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
140 homes
$600Ks
- $700Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
3.5 rating (2 reviews)
![Harvest Pointe]()
$800Ks
- $3Ms
Harvest Pointe, Cutchogue, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
124 homes
$500Ks
- $600Ks
Newbury Village, Brookfield, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
120 homes
Want to learn more about 55+ rental communities in Winsted, CT?
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Questions? Call us:
(860) 909-8066
Download the Ultimate 55+ Homebuying Guide
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$500Ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
108 homes
$400Ks
- $500Ks
O'Meara Farm, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 1998 - 2005
|
104 homes
$600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
$300Ks
- $400Ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$500Ks
- $400Ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
Want to learn more about 55+ communities in Winsted, CT?
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500Ks
- $600Ks
Founders Village, Southold, NY
Resale Only
|
55+ age-restricted
|
Built 1981 - 1985
|
92 homes
$300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
$500Ks
- $700Ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
5 rating (1 reviews)
![Paris Square]()
$400Ks
- $700Ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
Want to learn more about 55+ rental communities in Winsted, CT?
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$400Ks
The Village at Whispering...Rotterdam, NY
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
85 homes
Want to learn more about 55+ communities in Winsted, CT?
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Questions? Call us:
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5 rating (2 reviews)
![Benson Woods]()
$400Ks
- $600Ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
Park Glen
![10 HARMONY TRL # 10, NEW MILFORD, CT, 06..., New Milford, CT 06776]()
2 beds
|3 baths
|4,023 sq ft
|Condo
10 HARMONY TRL # 10, NEW MILFORD, CT, 06...
Community: Park Glen
MLS 24109997 • Coldwell Banker Realty, Erin Porte...
Oronoque Village
![766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
766 NYACK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24143831 • Coldwell Banker Realty, Christine ...
Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,575 sq ft
|Condo
195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24149127 • Property Choices Real Estate, Paul...
New
Regency at Woodbridge
![5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
5 WHISPER RIDGE WAY # 49, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24149933 • Thomas Jacovino, Kathy Childs
New
Heritage Village
![423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
423 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24147877 • KEY Real Estate Services LLC, Oliv...
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New
Oronoque Village
![315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,590 sq ft
|Condo
315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24148423 • eXp Realty, Tracey Jefferson
Oronoque Village
![151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
151 SOUTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24149480 • William Pitt Sotheby's Int'l, Erik...
New
Spring Lake Village
![889 GLACIER WAY # 889, SOUTHINGTON, CT, ..., Southington, CT 06489]()
3 beds
|2 baths
|1,923 sq ft
|Condo
889 GLACIER WAY # 889, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24149974 • Putnam Agency Real Estate LLC, Reb...
Rivington
![1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0..., Danbury, CT 06810]()
2 beds
|2 baths
|1,229 sq ft
|Condo
1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...
Community: Rivington
MLS 24141740 • Scalzo Real Estate, Adrienne Qui
Download the Ultimate 55+ Homebuying Guide
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O'Meara Farm
![2 CHERRY HILL CT # 2, FARMINGTON, CT, 06..., Farmington, CT 06032]()
3 beds
|3 baths
|2,062 sq ft
|Condo
2 CHERRY HILL CT # 2, FARMINGTON, CT, 06...
Community: O'Meara Farm
MLS 24146850 • Coldwell Banker Realty, Adam Canno...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Oronoque Village
![375 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,550 sq ft
|Condo
375 PIUTE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138198 • eXp Realty, Jeanne Varnum
Heritage Village
![335 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
335 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24147013 • Berkshire Hathaway NE Prop., Jacqu...
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24118807 • William Raveis Real Estate, Ron Ne...
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(860) 909-8066
New
Heritage Village
![813 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
813 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149937 • Berkshire Hathaway NE Prop., Bonni...
Heritage Village
![825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24124224 • Keller Williams Realty, Donna Doyl...
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New
Regency at Woodbridge
![3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24149912 • Thomas Jacovino, Kathy Childs
New
Regency at Woodbridge
![5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24149897 • Thomas Jacovino, Kathy Childs
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Oronoque Village
![164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139444 • Stacy Blake Realty LLC, Celina Cuo...
Regency at Woodbridge
![10 HILLCREST DR # 5, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
10 HILLCREST DR # 5, WOODBRIDGE, CT, 065...
Community: Regency at Woodbridge
MLS 24147212 • Thomas Jacovino, Kathy Childs
Heritage Village
![701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137961 • Coldwell Banker Realty, Claudia Fo...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Village
![69 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
69 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24133619 • Century 21 Bette Real Estate, Just...
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New
Oronoque Village
![446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614]()
3 beds
|3 baths
|1,426 sq ft
|Condo
446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
MLS 24147937 • Realty ONE Group Connect, Monica O...
Oronoque Village
![87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140020 • Oronoque Real Estate, Monica Dalto...
Oronoque Village
![289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,620 sq ft
|Condo
289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138784 • Oronoque Real Estate, Monica Dalto...
Oronoque Village
![617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24146302 • William Raveis Real Estate, Kenny ...
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Download the Ultimate 55+ Homebuying Guide
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Liberty at Newtown
![79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|3 baths
|2,317 sq ft
|Condo
79 SUZIE DR # 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
MLS 24148521 • Coldwell Banker Realty, Richelle W...
New
Heritage Village
![405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149715 • Mapleridge Realty, Tommy Dorso
Spring Lake Village
![811 VILLAGE RD # 811, SOUTHINGTON, CT, 0..., Southington, CT 06489]()
2 beds
|3 baths
|1,550 sq ft
|Condo
811 VILLAGE RD # 811, SOUTHINGTON, CT, 0...
Community: Spring Lake Village
MLS 24147874 • Coldwell Banker Realty, Elizabeth ...
The Village at Oxford Greens
![1119 ST ANDREWS DR 44, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,454 sq ft
|Condo
1119 ST ANDREWS DR 44, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24134811 • EG Group Realty LLC, Shabnam Sadat
The Village at Oxford Greens
![930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478]()
2 beds
|3 baths
|2,365 sq ft
930 TILLINGHAST DR # 930, OXFORD, CT, 06...
Community: The Village at Oxford Greens
MLS 24137749 • Real Estate Two, Karen Berwick
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Read the Ultimate 55+ Rental Guide
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Fairview at Oxford Greens
![1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
Community: Fairview at Oxford Greens
MLS 24110964 • EG Group Realty LLC, Shabnam Sadat
Fairview at Oxford Greens
![1119 ST ANDREWS DR 44, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,454 sq ft
|Condo
1119 ST ANDREWS DR 44, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24134811 • EG Group Realty LLC, Shabnam Sadat
The Village at Oxford Greens
![1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,..., Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1097 SAINT ANDREWS DR LOT 9, OXFORD, CT,...
Community: The Village at Oxford Greens
MLS 24110964 • EG Group Realty LLC, Shabnam Sadat
Heritage Village
![740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24116195 • William Raveis Real Estate, Daniel...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Heritage Village
![761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,063 sq ft
|Condo
761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24149158 • BHGRE Gaetano Marra Homes, Stephan...
Want to learn more about 55+ rental communities in Winsted, CT?
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Heritage Village
![1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24136244 • Dave Jones Realty, LLC, Gregory Mi...
Oronoque Village
![736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
736 QUINNIPIAC LN B, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24127108 • Coldwell Banker Realty, Larry Vecc...
Heritage Village
![60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
60 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137022 • William Raveis Real Estate, Ruth Z...
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Heritage Village
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24138526 • Showcase Realty, Inc., Gregory Bal...
Heritage Village
![876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
876 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139573 • William Raveis Real Estate, Ruth Z...
Frequently Asked Questions
In Winsted, there is 1 small community with less than 500 homes.
The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.
No, there are no gated 55+ communities in Winsted.
Want more information about active adult communities around Winsted?
Want to learn more about 55+ communities in Winsted?
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REIN updates its listings on a daily basis. Data last updated: Jan 21, 2026.
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